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Madison: Always Late (Part 2) - Hairbrush & Heartache 1 Madison: Always Late (Part 2) - Hairbrush & Heartache 2 Madison: Always Late (Part 2) - Hairbrush & Heartache 3 Madison: Always Late (Part 2) - Hairbrush & Heartache 4
Madison: Always Late (Part 2) - Hairbrush & Heartache
The Headmaster has reached his limit with perpetually late Madison. She is further punished with a hairbrush.
Updated: Mon. Dec. 16, 2019
Brooke: Yardstick Beatdown 1 Brooke: Yardstick Beatdown 2 Brooke: Yardstick Beatdown 3 Brooke: Yardstick Beatdown 4
Brooke: Yardstick Beatdown
Naked Brooke is made to bend over and grab her ankles for a long taste of the 'Yardstick of Doom, Pain and suffering'.
Updated: Fri. Dec. 13, 2019
Madison: Always Late (Part 1) 1 Madison: Always Late (Part 1) 2 Madison: Always Late (Part 1) 3 Madison: Always Late (Part 1) 4
Madison: Always Late (Part 1)
The Headmaster has reached his limit with perpetually late Madison. She is punished with face slaps and an angry OTK hand-spanking.
Updated: Wed. Dec. 11, 2019
Sadie: Home Again (Part 3) 1 Sadie: Home Again (Part 3) 2 Sadie: Home Again (Part 3) 3 Sadie: Home Again (Part 3) 4
Sadie: Home Again (Part 3)
Sadie's welcome home party continues with a long hard painful paddling on her already very well marked bottom.
Updated: Mon. Dec. 09, 2019
Sadie: Home Again (Part 2) 1 Sadie: Home Again (Part 2) 2 Sadie: Home Again (Part 2) 3 Sadie: Home Again (Part 2) 4
Sadie: Home Again (Part 2)
Sadie's welcome home party continues. The Headmaster orders her into a very strenuous and uncomfortable position for a hair brush spanking.
Updated: Fri. Dec. 06, 2019
Sadie: Home Again (Part 1) 1 Sadie: Home Again (Part 1) 2 Sadie: Home Again (Part 1) 3 Sadie: Home Again (Part 1) 4
Sadie: Home Again (Part 1)
Sadie has just been released from her drug rehab program. The Headmaster, feeling charitable and full of love for the world, decides to allow the little wayward junkie to return to his happy home of discipline and rules. She is welcomed back into the house with a naked strapping by the Headmaster (she is naked not him).
Updated: Wed. Dec. 04, 2019
Brooke: Yardstick and Hairbrush 1 Brooke: Yardstick and Hairbrush 2 Brooke: Yardstick and Hairbrush 3 Brooke: Yardstick and Hairbrush 4
Brooke: Yardstick and Hairbrush
Brooke is made to bend over for a spanking with the Headmaster's mighty yardstick. She is then ordered to change clothes and go once more over his knee for a spanking with a handy hairbrush.
Updated: Mon. Dec. 02, 2019
Daija: Paddle Paint Fail 1 Daija: Paddle Paint Fail 2 Daija: Paddle Paint Fail 3 Daija: Paddle Paint Fail 4
Daija: Paddle Paint Fail
The Headmaster inspects Daija's paint job on the new paddle and he is none too impressed. He orders her naked and on the floor for a aggressive bottom blistering paddling session.
Updated: Fri. Nov. 29, 2019
Sadie: Date Night! (Part 2) 1 Sadie: Date Night! (Part 2) 2 Sadie: Date Night! (Part 2) 3 Sadie: Date Night! (Part 2) 4
Sadie: Date Night! (Part 2)
Sadie prepares for a night out on the town with a gentleman caller. The Headmaster helps her to curb her 'whorish' ways with a brisk and spirited ass beating session carefully structured to keep her morals on point during the evenings festivities.
Updated: Wed. Nov. 27, 2019
Sadie: Date Night! (Part 1) 1 Sadie: Date Night! (Part 1) 2 Sadie: Date Night! (Part 1) 3 Sadie: Date Night! (Part 1) 4
Sadie: Date Night! (Part 1)
Sadie prepares for a night out on the town with a gentleman caller. The Headmaster helps her to curb her 'whorish' ways with a brisk and spirited ass beating session carefully structured to keep her morals on point during the evenings festivities.
Updated: Mon. Nov. 25, 2019
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